A mild and selective route to p-quinomethanes using dianisyltellurium oxide

Abstract

The o-quinones formed by chemical or enzymatic oxidation of 4-cyanomethylcatechols rapidly rearrange to isomeric p-quinomethanes which can be trapped: the structures of previously described 4-cyanomethyl-1,2-naphthoquinones are revised.

References

1. S. V. Ley, C. A. Meerholz and D. H. R. Barton, Tetrahedron, 1981, 37, 213.
2. J. Clews, C. J. Cooksey, P. J. Garratt, E. J. Land, C. A. Ramsden and P. A. Riley, Chem. Commun., 1998, 77.
3. C. J. Cooksey, P. J. Garratt, E. J. Land, S. Pavel, C. A. Ramsden, P. A. Riley and N. P. M. Smit, J. Biol. Chem., 1997, 272, 26 226.
4. A. Carlsson, H. Corrodi and B. Waldeck, Helv. Chim. Acta, 1963, 46, 2271.
5. P. A. Riley, E. J. Land and C. A. Ramsden, manuscript in preparation.
6. M. Gates and G. Tschudi, J. Am. Chem. Soc., 1956, 78, 1380.
7. M. Gates and W. F. Newhall, J. Am. Chem. Soc., 1948, 70, 2261.
8. M. Gates, R. B. Woodward, W. F. Newhall and R. Künzli, J. Am. Chem. Soc., 1950, 72, 1141.
9. A. B. Turner, Quart. Rev., 1964, 18, 347; W. M. Horspool, Quart. Rev., 1969, 23, 204; J. M. Bruce, in Rodd's Chemistry of Carbon Compounds, ed. S. Coffey, Elsevier, Amsterdam, 2nd edn., 1974, vol. III^B, p. 135; Supplement to Vol. III^B, ed. M. F. Ansell, 1981, p. 86; 2nd Supplement to Vol. III^B, ed. M. Sainsbury, 1995, p. 42.
10. M. Gregson, W. D. Ollis, B. T. Redman, I. O. Sutherland and H. H. Dietrichs, Chem. Comm., 1968, 1395.
11. E. S. Krol and J. L. Bolton, Chem. Biol. Interact., 1997, 104, 11; M. Sugumaran, S. Tan and H. L. Sun, Arch. Biochem. Biophys., 1996, 329, 175; M. Sugumaran, Pigment Cell Res., 1995, 8, 250; M. Sugumaran and J. Bolton, Biochem. Biophys. Res. Commun., 1995, 213, 469; M. Sugumaran and D. Ricketts, Arch. Insect Biochem. Physiol., 1995, 28, 17; M. Sugumaran, V. Semensi, B. Kalyanaraman, J. M. Bruce and E. J. Land, J. Biol. Chem., 1992, 267, 10 355.
12. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902.